4-Methylmorpholine → HCID 131718772, compound

HRID 741852Notes

Reaction equation

HRID 741852 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN1CCOCC1.[C:23]1(=[O:42])[N:27]([C@@H:28]([CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[C:29](O)=[O:30])[C:26](=[O:37])[C:25]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:24]12.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[C:26]1(=[O:37])[N:27]([CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][OH:36])[C:29]([NH:2][C@@H:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:30])[C:23](=[O:42])[C:24]2=[CH:41][CH:40]=[CH:39][CH:38]=[C:25]12

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 131718772HCID 131718772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of L-phenylalanine, ethyl ester, hydrochloride salt (998 mg., 4.3 mmol.) in dimethylformamide (10 ml.) was added 4-methylmorpholine (575 μl., 529 mg, 5.2 mmol). After stirring at room temperature for 5 minutes, the solution was cooled to 0° C. and treated successively with (S)-2-phthalimido-6-hydroxyhexanoic acid (1.002 g., 3.6 mmol.), hydroxybenzotriazole (582 mg., 4.3 mmol.), and ethyl-3-(3-dimethylamino)propyl carbodiimide, hydrochloride salt (770 mg., 4.0 mmol.). The resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 1.5 hours. The solution was partitioned between ethyl acetate and water and the organic extract was washed successively with 0.5N hydrochloric acid, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give 1.63 g. of essentially pure title product as an oil/foam. TLC (acetone:hexanes, 1:1) Rf =0.30.

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. stirringThe resulting mixture was stirred at 0° C. for 0.5 hour and at room temperature for 1.5 hours
  3. customThe solution was partitioned between ethyl acetate and water
  4. extractionthe organic extract
  5. washwas washed successively with 0.5N hydrochloric acid, water, 50% saturated sodium bicarbonate, and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customto give 1.63 g

Sources & evidence

ORD record
ord-e2633be0d76d461396f7975949b3b62b
Source dataset
uspto-grants-1996_09
Patent number
US05552397

Reaction notes

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